


Restraint

by Major_Fortune



Series: Widojest Smut [3]
Category: Critical Role (Web Series)
Genre: Blindfolds, Blow Jobs, Established Relationship, F/M, Grinding, Hand Jobs, Horseback Riding, Jealousy, Masturbation, Minor plot, Oral Sex, Orgasm Delay/Denial, PWP, Public Sex, Restraints, Semi-Public Sex, Sex Magic, Tail Sex, Teasing, Underwater Sex, Voyeurism, Widojest - Freeform, Widojest Week, bet, completely ignoring the prompts, inappropriate use of magic, minor beaujester
Language: English
Status: In-Progress
Published: 2020-07-08
Updated: 2020-11-07
Packaged: 2021-03-04 22:40:41
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 14,978
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25154104
Author URL: https://archiveofourown.org/users/Major_Fortune/pseuds/Major_Fortune
Summary: Caleb and Jester make a bet. A sex bet.Jester wants Caleb to teach her a complex spell but he's afraid she lacks the concentration required for it. Jester thinks he's exagerating and that his own self control isn't as good as he thinks.  They decide to make a bet, if Jester can make his control slip in under a week, Caleb will have to teach her.AKA   4 times Caleb was able to resist Jester + 1 time he wasn't(day 5 prompt - Teaching Spells)
Relationships: Jester Lavorre/Caleb Widogast
Series: Widojest Smut [3]
Series URL: https://archiveofourown.org/series/1494356
Comments: 15
Kudos: 186
Collections: Widojest Week 2020





	1. Temptation

**Author's Note:**

> Happy Widojest Week Everyone! This has nothing to do with the prompts (besides maybe nr 5 - Teaching Spells, but we're not on day 5 yet...) but I wanted to publish something to celebrate anyway. I've been seeing a lot of wholesome WJ fluff, so I needed to give back some smut to make up for it. Enjoy!  
> Kudos and Comments are always appreciated!

“I want to learn your hut spell.”

Caleb looked up from his book to see Jester leaning over his desk, tail raised in the air and swaying in a way Caleb knew meant trouble.

“What?”

She sat down, not on the perfectly nice chair in front of him but on top of the table. “The spell you use to create the dome we sleep in when we’re on the road. I want to learn it too.”

He smiled, closing his book and putting it down next to her. She moved over so she was right in front of him, practically sitting on his lap. “Are you trying to replace me, Lavorre?”

“Never. I just think it could be helpful, if we need to split up the group or if you run out of spells.”

“That is very smart of you, _Liebling._ ” He said, letting his hands roam up her smooth blue thighs. Sometimes he was still awestruck by the fact they were together, that this beautiful, colorful creature let him touch her like that. “But I’m afraid that spell is a little too hard for me to teach you.”

“Why??” She whined, pouting. Caleb fought the need to reach out and run his tongue over her full bottom lip.

“It is a very complex spell. It requires a lot of concentration and restraint to have it stay up for eight hours, even while you sleep.”

“Okaaay... I still don’t see why you can’t teach me.”

His hands roamed higher, slipping under the hem of her dress and she whimpered. Seconds later she had jumped down from the desk and straddled his lap, and they were making out in earnest, mouths and hands everywhere, clothes halfway undone. Only when Jester began trying to pull his shirt off did Caleb stop her by placing a gentle hand over hers.

“Because of this, _Liebe_.” He said, trying to catch his breath. “See how fast you forgot about the spell? If you lose focus with a kiss, how are you supposed to keep it in your sleep? Or in battle?”

Jester frowned, leaning back on his lap. “You lost it too! It takes two to make-out, Widogast!”

“It was always in the back of my mind, hence why I brought it up again.” He rubbed his blackened thumb over her bottom lip, trying to coax a smile out of her. Instead, she bit it gently. “Don’t be mad, Blueberry. I love how passionate and impulsive you are. It’s a wonderful thing! But it does make casting trickier and I don’t want you to get hurt if the spell backfires.”

“I’ve seen you be _preeety_ passionate and impulsive too, Cay-leb.” To make her point more obvious, she ground her hips against his, making him groan. “I think you’re overestimating your self-control.”

He pulled her in for a slow, gentle kiss. “I’m not great at many things, _Liebling._ But this, this I’m one hundred percent sure I excel at.” 

_“_ Alright, let’s bet on it, then!” She said.

“What do you have in mind?” Gods, he wished he hadn’t said anything and they had just kept making out. Damn him and his keen mind!

“One week! If you can keep your hands off me for a whole week, you win and I’ll admit you’re the self-control king or whatever.” She rolled her eyes. “But if you brake, you’ll have to teach me the spell.”

He chuckled. “One week? Is that it?”

“Yup. One week of no sex, no kissing, no touching at all. And that includes touching yourself, Widogast!”

“Easy.” He laughed again. “I was deprived of any touch for over a decade, one week will be nothing!”

She got up from his lap and started making her way out of the library, a trickster’s smile on her lips. “We’ll see. You didn’t know me before, you had no idea what you were missing.”

Caleb watched her leave, frustrated but also amused. He was certain of his ability to maintain control, but he was also sure that Jester would not make it easy for him. If her smile was any indication, she would make his week hell and enjoy every second of it.

*

The next morning, Caleb rolled over and found another body laying on his bed, next to him. Opening his eyes slowly, he saw Jester, head propped up on her arm, looking down at him in all her naked glory.

“Good morning, Cayyyy-leb.” She purred, trailing a hand down his bare chest.

“You’re up early, Blueberry. You didn’t sleep here last night, did you?”

She grinned, her hand dipping under the sheets to touch his lower abdomen. “No, but I woke up with a craving...”

“You know there are no donut shops in this town. And no, I already told you I don’t have a spell for making them.”

“Not that, silly.” She rolled her eyes. “I want you.”

Her nails grazed over his hip bone and Caleb’s cock stood at full attention.

“I need you, Cayleb.” She whispered in his ear, biting down on his earlobe.

Rolling over, he pushed her down onto the mattress gently and stood above her, between her open legs. Jester smiled like a cat cornering its prey.

That’s when Caleb remembered their last conversation.

“ _Wait_... is this about the bet?” He asked.

“ _Mayyyybe_.” She giggled.

“Jester...” It took all his strength to push himself away from her and get out of bed, but he did it. “Pouncing on me when I’m not fully awake is not fair. You’re playing dirty.”

She stretched her arms out, her luscious, curvy body taking over the entirety of his bed. “Oh, that was just my first try. It’s going to get a lot dirtier from here, Widogast.”

Caleb forced himself to stop staring at her and began getting dressed. “That should be against the rules.”

“Lucky for me, we didn’t establish any rules, did we? At least when it comes to what _I_ can and can’t do.” She smirked.

“That was clearly a mistake on my part.” When he was done, he grabbed a towel and made for the door. He expected her to get up and dressed as well, but she just watched him from the bed, smiling with sleepy satisfaction. “I’m going to take a bath. I’ll meet you downstairs for breakfast?”

She just gave him a noncommittal shrug and turned over, pushing her perfect ass in the air, tail swaying suggestively. “I’d rather just wait for you here. In case you change your mind while you bathe.”

*

Caleb took his time in the bath, first lathering his body and hair with the sweet honey and milk soap Jester liked and then submerging himself completely in the tub. The water slipped over the contours of his body, already starting to cool in the wintery Xhorhas air. It was chilly but not unpleasantly so, like the feel of a certain tiefling’s tongue as she made her way down his chest, agonizingly slowly. If he closed his eyes, he could still picture her in his bed, waiting for him...

Caleb fought the urge to touch himself. It was against their bet and, even though he knew she wouldn’t have known he had done it, he was too proud to go through with it. Cumming now would be admitting defeat, it would be knowing that she was right about his self-control. It had been less than a day, he couldn’t give up this easily!

He dried himself off and got dressed quickly, trying to get his mind to focus on other things like Dunamancy or the Nein’s next mission. But, by the time he got back to his room, he was still uncomfortably hard in his tight pants.

Things only got worse when he opened the door, however.

Jester, true to her word, was still in his bed. Except she was now sitting against the headboard, legs spread wide as she fingered herself.

“Welcome back, _Liebe._ ”

Caleb froze, one hand still gripping the doorknob. “What are you doing, Jester?”

“What you refused to do.” She said in a breathy voice. Her expert fingers continued to rub her clit, making her moan softly.

Caleb didn’t know if she hadn’t noticed the door was still open or if she simply didn’t care. He quickly slammed it shut.

“I told you I needed you.” She cupped her breast with her other hand, rubbing her thumb over and around her nipple. “This is all your fault.”

“Does this not go against our bet, _Schatz_?”

“Technically no, technically...” She whimpered, pinching her nipple. Caleb felt like he was going to die if he didn’t take his pants off soon. “We only agreed that you couldn’t touch yourself. _I_ can. I can even touch _you_ if I want to... Or you can just give up and help me with this.”

There was a voice screaming in his head, begging him to give in and join her. _This bet is ridiculous! End it, give up right now!_ It pleaded. _Look at her!_ Y _ou’re lucky you even get to see her like this! Yet here you are, denying her because of your ridiculous pride? Stop being an idiot, give in._

Caleb tried his best to ignore it. He made his way across the room and sat on his desk chair. He remembered leaving it turned towards the wall but _someone,_ had turned it towards his bed so he had a perfect view of what Jester was doing.

“I don’t think so, _Liebling._ I won’t break this easily.” He swallowed hard, trying to subtly adjust his pants. Looking down, his erection was ridiculously obvious, bulging out against his thigh. “But _you_ could end the bet. If you want me so desperately.”

Jester laughed, flashing sharp fangs. “I’m not a quitter, Widogast.”

“Then you’ll just have to do it by yourself.” He said, trying to tease her. But the low, breathless tone of his voice took the bite out of the words, betraying his inner struggle with his own libido.

“As you wish.”

Keeping her eyes on him, she brought her hand to her mouth and tasted herself, sucking on two fingers until they were dripping with spit. Then she trailed them down her body until she found the heat between her legs. She gently spread her folds, giving him a show, and stroked her clit once, twice, three times, her body shuddering with each touch. Only then did she push her fingers in, her eyes rolling back as she clenched around them.

Caleb knew Jester like to be watched, wanted, worshiped. This show was as much for their bet’s sake as it was for her own personal enjoyment. And, normally, he would be having the time of his life as well, leaning back in his chair and watching his gorgeous tiefling bring herself to the point of ecstasy and then shatter _oh so beautifully_. But the fact that he could not do anything about it, the fact that he was absolutely not in control, was driving him mad.

“Cayleb...” She moaned his name, her fingers moving slowly in and out. She was so wet already, dripping down her thick, freckled thighs and onto the sheets. “It feels so good! But I like your fingers better... Longer, thicker...”

Caleb’s nails dug into the wood of the armrests. “ _Gott im Himmel,_ Jester _..._ ”

At the sound of her name, slipping from his lips, a smile bloomed across her face. Her fingers started to move faster, her tail wrapped around her wrist as she ground the heel of her hand against her clit, her hips bucking in a frantic rhythm.

“Do you like watching me, Cayleb?”

All he could do was let out a strangled “ _Ja_...”

“I’m so close, baby _._ ” She keened. He could see her wrist flex as she curled her fingers inside her, her other hand kneading her breast. “Do you want to see me cum for you?”

Caleb knew he shouldn’t do it. He knew he should just stay still and quiet and not encourage her. But he couldn’t.

“Cum for me, Blueberry.” He ordered, his voice full of fake authority. She was the one in charge, he was completely at her mercy.

Jester’s lids lowered, her mouth slightly agape as she finger-fucked herself into a shuddering orgasm. She screamed his name as as she came, her body locking up and then falling apart, shaking through the aftermath.

Caleb’s mouth had gone dry. He was dying to climb into bed with her and hold her as she became a soft, satisfied mess in his arms. He was allowed to at least do that, right?

Apparently not.

Having come down from her post-orgasm bliss, Jester quickly got up and started getting dressed.

“Whe-Where are you going?” Caleb asked.

“Breakfast.” She said in a lilting voice. Then she turned around for him to lace up her bodice, which he promptly did, with shaking fingers. “This was fun.” She kissed his cheek, just the lightest brush of her lips against his feverish skin. “This week is going to be _sooo fun!_ ”

Before Caleb could even answer, she had walked out.

He was left shaking, raw and unfulfilled with just his memories of what had just happened and the echoing sound of her laughter as she walked away.

The rest of the day he barely saw her. She didn’t talk to him at meals and then disappeared into her room, like she was avoiding him. That was almost worst than the teasing. He had no idea what to expect and, even though not that much time had passed, he already missed her terribly.

His mind kept fighting between the idea that this was all part of her elaborate plan and the thought that she was actually mad at him. When night came, he laid in bed, sleepless and alone, for a long time. He didn’t know if this bet was worth it anymore. He didn’t know if his pride was either. This had all started as a joke but now he felt like they could easily take it too far and he could lose the best thing in his miserable life.

He had been able to deny her and survive his first day, but at what cost?


	2. Seduction

**Notes for the Chapter:**

> Hey guys, sorry this took so long, work gets in the way and I have about 10 other fic projects in the works at the moment. Don't worry if the next chapter takes a while, I'm finishing this no matter how long it takes. Also keep an eye out for another long multichapter widojest fic, coming soon ;)

They left the Xhorhaus early the next day, off to find another place the Wildmother had showed Caduceus, the menagerie of the Stone family.

They had left their moorbounders behind weeks ago so they were on horseback, the beasts kindly given to them by the Bright Queen. They had spent most of the day riding, so Caleb couldn’t really figure out if Jester was still being distant. She seemed happy enough, joking around with Nott and taking turns with Beau, reading passages of a cheesy romance novel Caleb had bought her back in Xhorhas, to pass the time. Whenever he asked her something she answered politely, but she wasn’t necessarily warm or loving towards him, barely spearing him a glace.

By the time the sun started to set and they found a clearing by a small lake to settled down for the night, Caleb was sure she was mad at him and it was driving him crazy.

Caduceus decided to make soup out of some wild mushrooms that grew on the trunk of one of the clearing’s trees for dinner and Caleb volunteered to gather the wood for the fire to keep his anxious mind busy. To his surprise, Jester immediately said she would go too, to watch his back in case there was something hiding in the woods.

For a while, they walked in complete silence, Jester skipping a few steps ahead, tail swishing from side to side. Every inch of Caleb’s body was on edge. Silence was never a good thing with Jester. He kept waiting for the storm to roll in, for her to break down and release whatever negative emotions she had been bottling up this entire time. Every second that passed without it happening only heightened his anxiety. When they reached a spot far away enough that the trees blocked their sight of the camp, Caleb couldn’t take it anymore.

“Are you mad at me?” He asked suddenly.

Jester turned around, her mouth opened in a pretty little _o._ “No...” She took two steps in his direction, close enough for him to talk without having to raise his voice but far enough away that he would have to reach out to touch her. “Should I be?”

“You’ve been... distant.”

She smiled and took another step. “Mama always said absence makes the heart grow fonder.”

Caleb let out the biggest sigh of relief, his shoulders slumping as the tension left him. “So this is still about the bet? You’re not really angry?”

She laughed. “No, silly.” She ran a hand down the front of his jacket, straightening his lapels. “But is it true? What Mama said. Did you miss me?”

“So much...” He whispered. “I have half a mind to push you up against that tree and take you right here, Lavorre.”

She grinned, her hand reaching up to grab a fistful of the hair at the nape of his neck and pull, just the way he liked. “You can. But you’ll lose the bet.”

Caleb had always known that Jester was perceptive and deceptively clever but he had never noticed how much attention she paid to all his tells, his soft spots, the things she did that made him weak. Turns out she knew them all and she wasn’t afraid to use that information to her advantage.

She got up on the tips of her toes and nuzzled her way inside his jacket to nibble at his neck, her tiny fangs digging in just enough to hurt. He groaned, his hands twitching at his side with the need to touch her. “Do you think it’s worth it?”

“You’re worth everything to me, _Liebling.”_ He told her, breathing hard as she started to suck a bruise into the side of his neck. “But I can’t give in this easily...”

She immediately let go, her lips leaving his skin with an obscene _pop. “_ You stubborn, stubborn man!” She huffed. “ _Now_ I actually have a reason to be mad at you.”

“But are you?”

She pouted and Caleb couldn’t help but smile. Even while angry she still looked ridiculously adorable. “No... I can’t get mad at you, Cay. You’re too cute.”

“You are... too good to be real, Jester.” He whispered, wishing desperately that he could kiss her. “But I need to complete this bet. I need to prove to myself that I can do it. I’m sorry, Blueberry.”

“You should be!” She poked the center of his chest, her sharp sparkly pink nail digging into his shirt. “You got my smallclothes all wet and now you’re not going to do anything about it? Not fair, Mr. Widogast.”

A shiver of pure, wild lust ran down Caleb spine and he almost cried out with want. “ _Sheisse_... You’re the one not playing fair. Do you know how much I miss your touch, your taste? It’s maddening!”

She giggled and gave his hair one more hard pull before stepping away. “Meet me by the lake, once everyone goes to sleep.”

“What do you have in mind?” He asked, eyebrow raised, wishing with every fiber of his being that she was planning to end the bet.

“You got me all dirty, now you have to help me clean up.” She shrugged, her eyes sparkling with mischief.

“How am I supposed to do that without touching you?”

“I have an idea, trust me.” She started to walk away skipping with excitement back towards camp.

“Wait!” Caleb called out after her. “What about the fire wood?”

“Didn’t you just refuse to let me touch _your_ wood? I think you can take care of that all by yourself.” She smirked, looking back at him over her shoulder.

“What if something comes out of the forest and attacks me?” He yelled back, feeling his cheeks heat up at her words.

“Just scream, I’m sure we’ll hear you.” She laughed.

“You’re ruthless, woman!”

“Yeah, but you love that, don’t you?” She said with a wink.

“Damn it...” He sighed. “I do!”

*

Despite his perfect memory, Caleb couldn’t tell what the group talked about during dinner. He couldn’t even remember what the soup tasted like or if he liked it although he knew he had finished it as fast as he could, trying to make sure the meal was over as fast as possible. He spend the entire time in an anxious daze, not able to stop himself from meeting Jester’s eyes across the fire and silently begging any God that would listen for everyone to go to bed straight after the meal.

Jester seemed to enjoy slowly driving him mad by how she grinned and licked her lips every time she caught him looking, she would casually lean forward to grab things out of her hoversack just so he could catch a glimpse of her cleavage and walk around the campfire, helping to clean up just so she could sneakily brush his body with her tail every time she passed him.

After everyone started setting up their bedrolls, Jester asked Beau if she could braid her hair and Caleb almost screamed in frustration. He huffily said that he was needed to get some sleep, hoping everyone else would get the hint, and laid on top of his roll, pretending to read despite not being able to focus. After what felt like forever, Jester and Beau’s laughter died down and he heard Beau shuffle into her bed while Jester’s steps got further and further away.

He took his time, making sure everyone around him was asleep or at least halfway there, specially Nott who was laying face down right beside him, snoring loudly. Only then did he put his book back in its holster and run towards the lake, trying to be as quiet as possible. When he got there, Jester was standing at the edge of the water in just her chemise, her bare feet splashing in the waves. There was a full moon out and it turned the lake into a silver mirror, bringing out the deep blues of Jester’s skin and hair and making her diamond tattoos glow. He walked forward in almost a trance, drawn to her like a moth to a flame, fuelled by the deadly need to touch her.

“You took so long getting here I thought you actually fell asleep.” She said, not bothering to turn around.

“Almost did after you decided to spend more time with Beauregard instead of sneaking off with me.” He reached the edge of the water and stood beside her, close but not enough to be tempted to touch her.

“Mr. Widogast, are you jealous?”

_Ja,_ he thought, _I’m jealous of anyone who gets to touch you right now._ “Just impatient.” He said instead.

“Really?” She finally turned towards him. “Impatient for what? You want to give up on the bet?”

“I thought _you_ were going to give up.”

She shook her head, laughing. “Me? I never give up, Cayleb. You should know that by now.”

She pulled her chemise down, letting it fall past her shoulder and hips until it pooled on the wet sand beneath her and she stood completely naked in front of him. If Caleb was a man with less composure he would have drooled. She looked even more stunning than he remembered.

“So you just invited me here to torture me?”

She pushed his coat down his shoulders and began working on the button of his shirt. “Is it torture if I know you’re going to enjoy it?”

“Will I? Even if I can’t touch?” He whined while she finished with his shirt and reached for the laces in the front of his trousers.

“Yeah, because _I_ can.” She giggled. “Give up control for once, Cayleb!”

He took a deep breath as she pulled his pants down, her eyes trained on his already half erect cock. “You know how difficult that is for me...”

Once he was fully naked, she backed away, walking backwards into the lake. “Well, you don’t have a choice this time. Unless you want to go back to bed...”

“I can’t do that... Not without you, at least.”

She grinned, submerged up to her waist. “Then follow me. And bring the soap.”

He looked around in confusion for a while until he found her dress on a rock along with a pink towel and a bar of soap. Jester had walked into the lake so easily he had almost convinced himself that despite the chilly weather the water must have been warm. It most definitely was not and he had to walk in slowly, hissing every time the water hit another part of his body.

“I’m _freezing_ , Jester.” He said, once he reached her.

“Don’t worry, I’ll get you nice and hot in a second.” She took the soap and started working up a lather. “Now where should I start?”

He expected her to begin washing herself but she planted her soapy hands on his chest, rubbing his pecks and shoulders with unusually precise, slow movements for someone as chaotic as her.

“Not that I’m complaining at all, but weren’t you the one who needed to get clean?” He asked as her hands started to trail lower, down to his stomach and what was laying beneath the water, steadily getting harder despite the cold.

“Yes, but unfortunately I forgot to bring a sponge, so you’ll have to do.” She washed him all the way down to his hips, her hands just barely avoiding his cock before she brought them back up and laced them around his neck. “Unlike you, I can do whatever I want. And what I want, Cayleb... is to use you for my pleasure.”

Before he could ask her what she meant by that, she pressed her luscious breasts against his chest, rubbing herself until she was as soapy as him. Caleb was helpless as she moved against him, not able to do anything but grunt and whine as she slipped and slid, teasing him with every touch.

“Warmer?” She asked, her hands travelling between them so she could palm her soapy breasts and pinch one of her nipples until she was moaning in his ear. Caleb had to dig his blunt nails into the palm of his hands to stop himself from grabbing her, he needed her so badly it made him want to scream.

“Getting there...” He sighed.

She giggled and turned around, laying her head on his shoulder to rub her back against his soapy chest now, very purposefully also rubbing her ass against his crotch. His cock slid deliciously between her soft, rounded cheeks and Caleb couldn’t hold back anymore, he cursed in the filthiest Zemnian he remembered, his voice echoing so loudly through the woods he was sure he had waken his friends up.

“Shhh!” Jester laughed and smacked his arm playfully. “They’re going to think I’m murdering you!”

“Aren’t you? I’m pretty sure frustration can kill.”

“I don’t think sponges are supposed to complain.” She stilled her hips, her spine curved as she pressed her ass hard against him, tail up in the air. “Do you want me to stop?”

“ _Nein, bitte!_ ” He cried out as she pulled away just the smallest bit. “I swear Jester, after this week is done I’m going to make up for every single second of torture you’re putting me through.”

“Yeah?” She asked, her voice almost a purr. “Tell me what you’re going to do to me.”

She ground her hips faster and his cock slipped down until he could feel the slippery heat of her cunt, just barely brushing against his head. He was so close, one push and he could be inside her... it was unbearably tempting. 

“Oh fuck, _Kätzchen_...”

“Tell me.” She insisted, pressing her thighs together to trap him between them as she rubbed herself on his cock. Even under water she could feel her hot slick coating him, making her thighs even more slippery, the friction delicious.

Caleb leaned against her, worrying for a moment that he was going against the unclear rules of their bet. But Jester didn’t say anything, too wrapped up in what she was doing under water, and he buried his face in her hair. Gods, she smelled amazing, like warm cinnamon rolls and winter mornings and home... She was his home and he was terribly homesick. How long had it been since he had kissed her? One day? Two? Far too long.

“First, I’m going to kiss you until your lips go numb.” Jester pushed back against him until his cock rubbed against her clit and keened, her tail wrapping around Caleb’s middle to steady her as she picked up speed. “Then I’m going to kidnap you and keep you in my bed. I don’t care who comes knocking or how much time passes, I won’t give you up. I’m going to touch and taste every single part of your beautiful body, to remind you of what you’ve been missing.” Jester shivered against him, her breathing fast and shallow. “And then? Do you know what I’m going to do then?”

“W- _Oh Gods..._ What?” She moaned.

“Remember that night I made you cum five times?”

“ _Six._ ” She hissed, he body going stiff in a tell-tale sign that she was close to climax.

“Hmmm _ja..._ ” He hummed, knowing he was also dangerously near the edge. “I’m going to break that record. Several times over.”

“Fuck _yes_! _Please!”_ She pleaded. “Shit, I’m so close...”

“So am I...” He whispered back.

“You know that if you cum you’ll lose the bet, right?”

Caleb groaned, closing his eyes tightly. “Then we need to stop this now...”

“What about all your self control?” She teased, grinding down harder.

“ _Sheisse_!” He had to take a deep breath to steady himself. “I’m just a human man Jester, I can keep my mind focused but I can only control my body to a certain point.”

She stuck her tongue out at him. “If you want me to stop you need to ask me. I want to hear you say it, word by word.”

Clenching his jaw, Caleb forced the words out. “Jester, as much as I’m loving this, I want you... I want you to stop touching me.”

She stopped immediately and stepped away from him, delving a little deeper into the lake. The absence of her touch was physically painful and he gasped as, without her heat around him, the cold of the water seeped back into his skin, enveloping his cock in an icy grip. Like in all other aspects of his life, Jester’s absence was the difference between him being in Heaven or Hell.

“Happy, party pooper?” Jester pouted, crouching down until the water reached her chin. “Now no one gets to cum.”

Caleb eyed her for a moment as she began to actually wash herself with the bar of soap, trying to regain his composure. It didn’t take him long to come up with a plan, as worked up as she had left him. “Maybe you still can.”

She carelessly dropped the soap, letting it sink into the bottom of the lake, her eyes trained on him, still hungry and darkened with lust. “What do you have in mind, Cayleb?”

He came closer, just enough to bend down until he was at eye level with her crouching form. “Use me some more... I can’t move, but you can fuck yourself on my fingers, if you’re willing to do all the work.”

She squealed with delight, jumping up from the water. “You’ll let me do that? It’s only going to make you more frustrated...”

“I don’t care.” He shook his head. “Just being able to watch you is a pleasure.”

She wrapped her arms around his neck again and gave him a big kiss on the cheek. “Don’t think I’m going to go easy on you for the rest of the week just because you’re being so good.”

“Wouldn’t dream of it.” He chuckled. “Now, do you want to start slow? One finger?”

She bit her lip. “Two, please. I’m _super_ ready.”

“Whatever my _Liebling_ needs.”

Positioning without him moving was tricky but they managed it with Jester guiding him by the wrist until she was straddling his arm, her tail wrapped around his forearm to keep him in place. She lowered herself and his fingers slipped in easily, her wet cunt taking him in with no resistance. Jester moaned his name and began riding his hand hard and fast, chasing the climax he had interrupted before. Caleb had to fight the will to move, to curl his digits inside her and find that spot that made her eyes roll to the back of her head. She didn’t need his help, that was very evident by how she angled her back and curled one leg around his waist to better position herself, one of her hands dipping down to play with her clit. But Caleb wanted to play a bigger part in this, so he did the one thing he knew she loved in bed that didn’t involve him moving a single limb, he started whispering to her in Zemnian, mixing sweet compliments with dirty promises of what he would do to her. Jester didn’t know Zemnian besides a couple of little things he had taught her, like numbers and colors, but she loved hearing him speak in his native language, it never failed to turn her on.

“Fuck, that’s so hot, Cay!” She panted, digging the nails of her free hand into his back.

“ _Wir du für mich kommen, Liebling?”_ He purred in her ear.

She nodded frantically, her eyes glassy and mouth parted as she uttered a series of quiet, incoherent prayers. She thrusted down hard on more time and Caleb felt her fall apart around his fingers, her cunt quivering as she came in his arms. She let go of him slowly, untangling their limbs and making sure she was steady on her feet before unwrapping her tail.

“Was that good?”

“ _So_ good, baby!” She giggled. “Maybe good enough for me to give you a break tomorrow...”

“Don’t you dare, I want to win this fair and square!”

She grinned. “Good. That was a trick question and you totally passed! Now let’s get out before you catch a cold.”

She took him by the hand and guided him back to where her clothes were, they shared the towel and got dressed again, Jester’s eyes growing heavier by the second.

“I wish I could sleep with you, Blueberry.” He said as they began walking back to camp.

“Well, you can always cuddle up to Nott.” She joked with a yawn.

“Not in this state I can’t!” He pointed down at his pants, where his still half hard, unsatisfied dick, was visible through the fabric.

She giggled sleepily. “Frumpkin then. I don’t think he’ll mind.”

“ _Ja_ , he’s the only one who never judges my sorry states.” He sighed. “What about you? Will you be able to sleep with the cold?”

“Sure, I’ll just spoon Beau.” Caleb didn’t say anything but he couldn’t stop the frown that took over his face and she saw it clearly. “Don’t be jealous, Cayleb! She’s my best friend!”

Oh, but he _was_ , he couldn’t help it. He was Beauregard’s friend too and he noticed the way she looked at Jester, the dopey smile that bloomed across her face when they talked, the way she instinctively tracked her in battle, wanting to keep her safe. Exactly like he did. Because they were both in love with Jester Lavorre. He had just been lucky enough to catch her eye first.

“And what am _I_?” He asked her.

She got up on the tips of her toes and gave him a peck on the lips, even though she knew he couldn’t kiss her back. “You’re my heart. My whole heart, Cayleb.”

After that, all complaints left his mind. He went to sleep with an awkward boner in his pants and an unhappy Fey cat pressed to his chest, but also the biggest smile in the world on his face.


	3. Damnation

**Notes for the Chapter:**

> Heyyyy, so I know I'm literally the worst and I took two million years to update this... but we got here in the end!  
> I've gone back to work at the office (despite the clear rise in infection nmbrs in my country everything is open again...) which really cut on my writing and cosplay time. Also, not gonna lie, this chapter got away from me, I had an idea then totally lost interest in it and had to think of something else for the chapter. Don't worry, the next one is already mapped out and shouldn't take this long.  
> Comments and Kudos are always apreciated!

They continued their journey the next day and, soon enough, the forest started to thin out and give way to arid, deserted plains. They spent half of the next day making their way trough the desert until they found a cave.

Cad was the most hesitant of them all when it came to entering the large rock formation. He had been the one to receive the message from the Wildmother but, from what he could recall, there was something off about it.

They entered the cave anyway, curiosity wining out over caution and rational thought. What they found inside, though, was nothing but utter chaos.

The cave was not a menagerie, at least not anymore. The paintings on the cave walls proved that the place had definitely been a place of rest for the dead once but, either the Stones had ended their holy mission, or they had been forced to go somewhere else.

The cave was not empty, however. As they delved deeper, they found a large Orc tribe. At first, they tried to fight, but they were severely outnumbered, so they decided to run. At the cave entrance, Caduceus used Move Earth to close them in. From inside, the Orcs banged on the wall, sending dust and pebbles flying around. They knew the wall wouldn’t hold out for long, they needed to get back on the road, fast.

They climbed back on their horses, with Cad in the front and Caleb and Nott taking the rear, Jester and Beau riding right ahead of them in case someone needed healing. Jester started straddling her horse when she seemed to have a better idea. Hopping down, she made her way to Caleb and Nott.

“Nott, let me ride with Cayleb.” Jester told the goblin, petting their horse’s mane. “I’ll keep him safe if the Orcs get out.”

“You don’t have to, Jester. I can handle it, I have my crossbow and-”

“ _Pleaaase_?” Jester interrupted. “I promise I wont let anything happen to our squishy wizard.”

Nott gave her a look of amused mistrust, her eyes going from her to Caleb and back again. When the wizard smiled at her, she shrugged and made her way to Beau’s horse.

“Are you that worried about me, _Liebling_?” Caleb asked as she climbed up behind him and wrapped her arms around his waist.

“Well, you _are_ super squishy, Cayleb.” They started to move, their horse close to the others but far enough that no one else could hear their hushed conversation. “But that isn’t the only reason why I asked to ride with you...”

He laughed. “I figured as much.”

“You know, I had a _really_ good time last night.” She pushed his hair and scarf away from his neck so she could kiss it. “But I couldn’t stop thinking about how unfair it was that I got to have all the fun.”

“Not _all_ of it. I also enjoyed myself quite a lot, Blueberry.”

Caleb could feel her smiling wickedly against his skin. “I still think you deserve a reward.”

“Is that your way of saying you’re ending the bet?”

“What would be the fun in that?” She giggled and tightened her arms around him, her mouth hot against his jugular. “No, I’m not going to be a spoil sport.”

“This is starting to sound more like another test of my will rather than a reward.”

“Maybe it’s both. You did tell me not to go easy on you.” 

“I’m often the orchestrator of my own misery.” Caleb said, trying to keep focused on the road ahead even as she gently grazed her fangs down the side of his throat. “But go ahead, don’t let my suffering stop you.”

“Are you trying to use reverse psychology on me?”

“ _Nein_... unless it’s working.”

Jester laughed heartily and slipped a hand under the hem of his shirt, feeling his lean stomach. He was definitely not as thin as he had been when he first joined them, his ribs didn’t stick out anymore and he had even grown a little stronger but he didn’t have defined abs or anything of the sort. Jester didn’t seem to mind, though. “It’s definitely not.”

“So...” He inhaled sharply, feeling her nails scrape across his chest as she kissed his neck. “...what do you have planned for me?”

“Oh, _sooo_ many things! You don’t even know the stuff _I_ want to do once this week is over... You’re not the only one with plans.”

“You know we could do those things a lot quicker if you ended the bet.”

“I’m aware. But it’s still going to be a no.” She said as she licked a stripe up his neck. “Besides, I left all my fun new toys back in the Xhorhaus.”

“You got new toys?” He asked quietly, his mind filling with wonderful possibilities. For someone who was a virgin when they first got together, Jester had learned an awful lot about sex and all kinds of kink from her mother and Caleb was thoroughly enjoying exploring those options with her.

“Yup! What do you think I was up to the day before we left Rosohna?”

“Avoiding me? Driving me crazy with worry?”

She giggled. “Well, yeah. But I also went shopping with Beau and Yasha and we found a store that sells lots of fun little things...”

“Like what?”

“I’m going to keep most of them a secret but I’ll tell you about my favourite.” She let her hand drift lower inside his shirt, her fingers dancing right above the waistband of his pants in a way that promised trouble. “There’s a ring that allows me to make a corporeal duplicate that lasts 30 minutes. Ever wanted to fuck two of me at once?”

Caleb’s only answer was a low groan and Jester bit down on the tender spot between his neck and shoulder forcing a sharp exhale out of him as his cock hardened in his pants.

“ _Sheisse_...”

“That wasn’t an answer. Use your words, Widogast. Unless you don’t want to do it...” She let her sentence hang in the air like a threat, her fingers lifting off his skin, ever so slightly.

“ _Nein, nein!_ I do! Gods, I really do...That sounds amazing!”

“Yeah?” She teased. “I’m not convinced. Maybe you should try a little harder to show me how much you want it.”

“ _Bitte, Liebling_...” He begged without hesitation, his cheeks reddening with embarrassment. In just a couple of days she had made him so desperate for her that pleading seemed like the least he could do for a chance to touch her again. He knew he was still winning the bet at that point, but it sure didn’t feel like it. “I want it very, very much. Tell me what it will take to convince you. I’ll do it.”

“Even if I ask you to end the bet?”

Caleb froze, he knew a trap when he saw one. “Except that. Anything else.”

“Perfect. Because that’s not what I want at all.” She laughed with a delight that sent shivers down Caleb’s spine. He was definitely in trouble. “I just want to cast Blindness on you.”

“What?” Caleb asked, completely dumbfounded for once. “You want to... blind me?”

“Just for a little bit. I want to try something out... I want you completely at my mercy.” She giggled and Caleb swallowed hard, both intrigued and frightened. As the only human in the party that didn’t have a way to see in the dark, he knew how debilitating blindness could be.

“But I’m guiding the horse!” He argued halfheartedly.

Jester shrugged, he couldn’t see it but he felt her move, her chest rubbing against his back. “I can take the reins. Don’t you trust me, Cayleb?”

The whine in her voice as she said his name almost undid him. Despite all the teasing and laughter, he could tell Jester was more unsure with him now. This bet was messing with her head almost as much as it messed with his. This wasn’t just a sexy little test of his self-control, she wanted him to trust her now because he hadn’t before, with the spell. He hadn’t trusted her to take it seriously and keep herself safe. He was such a fool...

“I do. There’s no one else in the world I trust more, not even myself. Please tell me you know that, Jester!”

Jester sniffled and Caleb’s heart tightened in his chest. He was never going to forgive himself for this. He knew right then and there that, win or lose, he was going to teach her the spell. He would teach her all of the spells he knew, if she wanted. He would do whatever it took to make sure she never had to wonder again if she had his trust.

“I-I do...” She said, her voice a little shaky, before she cleared her throat and put on her usual well rehearsed cheerful tone. “Does that mean I can blind you?”

Caleb sighed. “ _Ja_ , if it is what you want...”

She kissed his cheek softly, the hand under his shit just pressing against his skin, comfortingly. “Try to relax. I’m going to make this fun, I promise!”

He felt her shuffle around, looking for her symbol of the Traveler before she started casting the spell. Caleb felt the darkness start to tinge the edges of his vision and didn’t try to resist it, doing his best to follow her advice and relax. When he became fully blind, however, panic started to take over.

He was very much not having fun.

Without sight, he became hyper aware of his other senses, the sound of wild birds flying above, the smell of the horse beneath him and the feeling of his own body sliding dangerously now that he couldn’t use his vision to keep his balance. He had never felt more fragile and human, they could get attacked at any moment and he would be the easiest prey.

“Shhh, you’re okay.” Jester cooed, taking the reins from his hand and rubbing his stomach in small, soothing circles. “Just take a nice, deep breath.”

Caleb hadn’t even realized he had started hyperventilating. “I feel very vulnerable right now...”

Jester pressed herself harder against, letting him feel her warmth but also her strength, keeping him centered on the horse. “I’ve got you, baby. I won’t let anything happen to you. Anything bad, anyway...”

“I-I know that... I just don’t like feeling this helpless.”

“Well, you being vulnerable for once is kind of the point of this experiment.” Jester’s fingers started drawing patterns along the skin of his stomach and chest. “But if it’s really freaking you out we can stop it... I can use greater restoration to-”

“ _Nein_ , I want to try it.” He interrupted her. “For you, I’ll try it.”

“Awesome!” She squealed. “But if you change your mind later, let me know right away, okay?”

“Ja, of course.”The horse walked over something lumpy on the road and Caleb lurched forward but Jester grabbed the back of his jacket and pulled him back. “Oh shit, what was that? Are you sure you can guide the horse? Can you even see the road from back there?”

“Cayleb, hush.” Jester said in a surprisingly stern voice. “I told you not to worry. That’s my problem now and I’ve got it handled.”

“Right, right, I’m sorry...”

She pulled his scarf off and went back to kissing and nuzzling his neck. Every touch felt strangely heightened, her kisses made him shiver, her breath on his skin peppered it with goosebumps. But the warmth of her body behind him was familiar and grounding and the way she lavished what little skin she could reach with care and attention was so comforting Caleb found himself actually relaxing, his body going limp against hers, except for his cock which was hard again, straining against the fabric of his pants.

“How do you feel now?” She asked, nibbling on his earlobe.

“Better... and very turned on.”

“Oh, _I_ can seethat. Those are some _very_ tight pants, Cayleb.” Jester giggled. “Sooo... there’s something else I want to do.”

 _In for a copper, in for a platinum..._ Caleb thought. “What is it?”

“Let me tie your hands.”

Caleb laughed. Even if his control broke and he wanted to reach for her, there was not much he could grab in this position, bound or not. “Why? It’s not like I can touch anything anyway.”

“Indulge me.” She whispered in his ear.

“Don’t I always?” He purred back.

She took his jacket off and pulled his arms behind his back. As she moved him into the position she wanted, Caleb felt his hands brush through fabric, rubbing against the lace and silk of Jester’s dress and petticoats, until they were buried under it all. He felt the heat between her legs, the tips of his fingers just barely touching one smooth thigh as Jester tied his wool scarf around his wrists with surprising efficiency.

She wiggled around as she tested the knots and Caleb felt something new against his finger tips, warm, wet lacy fabric. Jester groaned and that’s when Caleb finally understood what her plan was. She was giving him a way to cheat, a way for him to touch her without breaking the rules of their bet.

“Clever, _Kätzchen!_ ” He grinned and moved his fingers, trying to find her clit by touch alone.

“I know I am but...” She sighed as he hit the spot. “Mr. Widogast, what do you think you’re doing?”

“What does it look like I’m doing?”

“Losing a bet.” She said, even as she bucked her hips shamelessly against his touch.

“Really? And here I thought I was just adjusting my hand before it lost circulation...”

“Oh, _that’s_ what you were doing? Then you’re perfectly fine! Please continue!” She said in her most innocent tone and Caleb rewarded her by applying more pressure.

Jester buried her face in the crook of his neck, muffling a moan. She placed the hand she was using to hold the reins on his thigh, but the other one found its way to the front of his pants. Without his sight, Caleb couldn’t tell what she was going to touch next and almost kicked the horse when she stroked his cock through the thick fabric.

“Jester...” He keened.

“Shhh! You have to be quiet, Cay.” Her hand slipped inside his pants and he bit his lip so hard he could taste blood trying to hold back his moans. Gods, how he missed her touch, the way her small fingers wrapped around him. “You don’t want them to see us like this, do you?”

“ _Nein_...” He gasped, his cock twitching in her hand, his own fingers stopping their movements under Jester’s skirt.

“Your mouth is saying no, but you dick seems _pretty_ excited about the idea. Naughty, Mr. Widogast!”

“Blueberry... Don’t tease me, there’s only so much my human heart can take.”

“Oh but teasing you is so much fun!” She pulled his cock completely out of his pants and started stroking it slowly. “Besides, if one of them happens to turn around and see us, we have nothing to be ashamed of. We’re, like, really hot!”

“I would still prefer to keep my private parts... private.”

Without warning her hand vanished and Caleb hissed quietly at the lack of contact. He heard something wet just behind his left ear and then felt her hand return, warm and spit slicked. She started pumping him faster and he almost came right then and there. He had to take some long, meditative breaths and recite the schools of magic in his head about 10 times before he felt himself regain control.

“But you have such a nice dick, Cayleb! Trust me, I’ve seen a lot of them and yours is like, one of the prettiest.” Jester whispered in his ear. “And it also feels so good inside me...”

She moaned and Caleb felt something else brush past his hand and rub at her cunt, something smooth and long.

“Are... are you touching yourself with your tail?”

Jester giggled. “Yeah. All this talk about cocks made me feel so empty... If I can’t have you inside me, this is the next best thing.”

Her tail moved under his hand, pushing the edge of her underwear aside and sliding into her. Jester keened as she slowly took in the large heart shaped tip of her tail, her hand continuously stroking Caleb. He wished he could see it but he had witnessed it enough times for his mind to fill in the blanks, the absolutely obscene sounds of her slick adding to the mental image in a way that was dangerously stimulating.

“ _Meine Götter_ _Schatz_ , it’s almost worse than being able to see it!”

“Are you picturing it in your head?” She hummed against the back of his neck. “I love how creative you can be with that perfect memory of yours. Picture me naked so it’s hotter, with my hair all wild and my boobs bouncing every time the horse jumps over something.”

As soon as she said it, he saw it in his mind, of course. The image was so detailed, taken from all the little memories he had of her body, it could have been real and it made his entire being ache with _need._

“It was pretty hot already.” He whined. “I could have pictured you in full Crown’s Guard armor and it would still turn me on, Blueberry.”

“Kinky... Maybe I can ask Essek to get me a set when we return.” She said, her thumb running over the head of his cock to collect his leaking precum. Caleb shivered, still in control, but just barely. “Are you going to cum having dirty thoughts about me, Cay?”

“It wouldn’t have been the first time, _Liebling._ But no, I don’t intend on losing just yet.”

“Bummer, I guess I’ll have to finish all by myself.” Her tail started to move faster, brushing Caleb’s hands every time it went in and out of her, coating his fingertips with her slick. “How are your hands, by the way? You haven’t moved them in a while and I don’t want you to lose circulation.”

Caleb got the hint and began rubbing her clit again, with her tail pushing her undergarments aside he had full access to her cunt and the temptation to let his fingers join her tail inside was almost too much to resist. She tried to keep stroking him as Caleb played with her, attempting one final time to get his restraint to break before she fell apart. But the effort of controlling her tail and her hands as she approached climax was too much and she just held on to him as she came with a broken cry.

Even without the friction, just feeling Jester around him and hearing the sounds she made almost did Caleb in as well but he managed to hold on by reciting the last chapter of the book Essek had lent him in his head, translating it to Zemnian from the original Undercommon. His cock twitched in her palm, needy and unsatisfied, but under control.

Jester wrapped herself around him in the afterglow, tucking her head into the crook of his shoulder and just laying there until her breathing calmed down. When she finally straightened up, she gasped softly in Caleb’s ear and then started laughing.

“Jester?” She didn’t answer him, just hid her face in his shoulder and tried to stifle her laughter. “ _Liebling_ , are you okay? What happened? You’re worrying me...”

“I may have been a little too loud... Pretty sure someone saw us.”

Caleb’s went completely stiff, shame washing over him like ice water as he remembered that his cock was still on display in her hand. He rushed to tuck himself inside his pants only to realize his hands were still tied up. Jester took pity on him and did it for him, laughing all the way.

“Who was it?” He asked.

“I’m not going to tell you, you’ll just freak out!”

Like he wasn’t freaking out already!

He started going through the options, from least to most concerning.

Yasha would not care at all if she saw it, she would look away quickly and never talk about it.

Fjord would probably be as embarrassed as Caleb was and wouldn’t bring it up, unless he got too drunk and let it slip.

Caduceus always noticed everything, which meant the likelihood of him seeing it was high but, while he sometimes let out a couple of sly remarks, they were usually so subtle the others would never know what he was talking about.

Nott seeing him and Jester like that was absolutely mortifying, like having his mother walk in on him masturbating.

But Beau... Beau would be the worst of them all. She would never, ever, let him live it down.

“Please, please, tell me it wasn’t Beau...”

Jester laughed even harder and Caleb considered if dying of embarrassment really was just a figure of speech.

“That’s it, I’m running away and living in the woods.” He groaned. He would have hid his face in his hands but without sight there was no point, darkness couldn’t keep the shame away. “Becoming a hermit seems less awful than having Beauregard bring this up over and over again for as long as I live.”

“What about me? Are you leaving me behind?” She asked, clearly only half joking.

Caleb huffed. “I couldn’t possibly ask you to leave this life for one of isolation.”

“Doesn’t sound that bad... we could have a little cottage, I’d paint, you’d read.” She sighed dreamily. “We could change our names and make up backstories. I’d be Fiona Fancy Pants, of course. I could say I’m your wife and we eloped to get away from the nobleman my family wanted me to marry...”

She blabbed on about their possible fake life but Caleb couldn’t hear anything after she said she would be his wife. He knew she was only joking but even the idea of pretending to marry Jester made him so ridiculously happy his chest ached.

“Would you like that? Being my wife?” He interrupted.

She was quiet for a little bit and, even without sight, Caleb knew she was chewing on her bottom lip like she always did when she was unsure of what to say or afraid that she had said too much.

“You mean, like, pretending?” She muttered almost too quietly for him to hear.

Caleb turned his head, towards her. “ _Nein_...”

Jester’s mouth fell open but no words came out and Caleb was startled to realize he could see it. His vision came back slowly, shadowy and indistinct at first, so all that he could see was Jester’s face, but that was alright because there was nothing else in the world he wanted to gaze upon more.

“Gods, you’re beautiful!”

“You can see again!” She grinned, their earlier topic of conversation forgotten for the time being. “How was it, being touched in the dark?”

“...Surprisingly effective.” He admitted. “You almost got me. Almost. What gave you the idea? A book?”

“Nope. Yasha, actually. She suggested using a blindfold but what would be the fun of that?”

Caleb almost choked. He hoped this had come up randomly in conversation when they went to the shop in Roshona and that she hadn’t actually discussed their sex life with their friends.

“Yeah, Beau was pretty shocked too. Don’t know why, Yasha’s wardrobe is 90% leather and chains, she had to at least be a _little_ kinky.”

“Let me guess, Beau ended up buying a blindfold on your little trip.”

Jester giggled. “Nope. She just kept _casually_ bringing up that the sashes on her Cobalt Soul uniform would make great blindfolds.”

“Maybe if I tease her about that when she brings this up and she’ll shut up about it...”

“Cayleb,” Jester said, a smirk still on her face. “I was kidding before. Beau didn’t see us. No one did.”

“Really?” All of Caleb’s breath left his body in a relieved huff. “Oh, thank the Gods! _Liebling,_ You’re going to give me a heart attack one of these days...”

“Don’t be so dramatic! You weren’t _that_ freaked out by it. You’re still hard.”

Caleb looked down even though he didn’t have to to know she was right. Damn it, he really needed to get some looser pants... He just hoped it went down before he had to get off the horse and someone else noticed. It was hard to believe Jester had managed to get herself off and almost do the same for him completely unnoticed but his ridiculous trouser tent was going to be the thing that gave them away. Except, there was something about that which didn’t make sense to him...

“Wait... if no one saw us, why did you gasp?” As much as Jester love playing pranks, Caleb could always tell when she was lying. Her gasp had been real, Caleb had pulled that sweet sound from her lips enough times to know that much.

“Oh that’s because I looked behind us and I saw the Orcs were coming.” Jester said like it was the least concerning thing in the world.

“The _Orcs_ are coming?” He asked in a much more concerned tone. Looking behind them, he noticed that, in fact, not only were they coming but they were getting far too close for comfort. “And you didn’t warn us about it?”

Jester pouted. “In my defense, they were a lot further away than they are now. Also, my mind wasn’t that clear at the time... Which is kind of your fault.”

“I would say it’s your tail’s fault, actually.”

“If you gave up the bet like I wanted, I wouldn’t have had to use my tail.” She huffed.

“I think we’re losing the point here...”

“Which is?”

“The Orcs, Blueberry?” He sounded exasperated but he couldn’t help but smile as he looked back at her over his shoulder.

“Right, right! I’m going to warn the others...” She grabbed on to his shoulders to lift herself up as she called out to their fiends but, before she spoke, she sat back down. “Hmm... Maybe I should untie your hands before we do that”

Caleb felt his cheeks redden, he had gotten far too comfortable with his restraints. “ _Ja_... I think that would be advisable.”

“Wouldn’t want anyone to accuse us of being up to no good back here...” She joked, kissing his neck one last time as she untied him. Caleb put his jacket back on, closing it up to hide what was still going on in his pants.

“You’re aware that I’m going to get you back for all of this, aren’t you?”

“Oh babe _,_ ” She laughed. “I’m counting on it.”


	4. Downfall

Caleb wished he could say the fight against the Orcs had been easy.

It was not.

Beau had gone unconscious, Yasha had been badly wounded and Jester and Caduceus had to use every single one of their healing spells. To say that the trip back had been rough was an understatement. Fortunately, it was also relatively short, they were back to Roshona in little over a day and a half.

As expected, Jester hadn’t been in the mood to keep up her attempts to tempt him into losing the bet during the rest of the trip and, once they got home, they were both too exhausted to do anything other than bathe and crash in their own beds, alone.

The next morning, however, Caleb woke up feeling surprisingly refreshed. Sleeping in a proper bed after days of bedrolls and horseback riding did wonders for both his back and his mood. So, when he received a message from Essek asking him if he was feeling well enough for a Dunamancy lesson, he answered back eagerly. They scheduled their class for the afternoon, in Caleb’s study, as usual. That left him enough time to get some reading done and enjoy lunch before Essek arrived.

It also left him enough time to worry, since he didn’t see Jester at all that morning. During the early hours, he expected her to sneak into the study to spend some time sketching beside him, like she usually did. When she didn’t show up he simply thought she must have been sleeping in, making up for the restless nights on the road. But when she didn’t come to lunch either, he started to grow concerned. They were home so he knew she was physically safe but her mood had been unstable lately so he couldn’t be sure if she was retreating to hide her sadness, or if she was preparing something to do with him and their bet. Either way, Caleb was left unsure of what to do and that was not a position he liked to be in.

He asked Beau about her, but she said she had been working out all morning and when she had last seen Jester, she was still asleep. A quick trip to their bedroom, though, proved that she was no longer there.

He saw Nott going up the stairs as he left Jester’s bedroom and stopped her in her tracks.

“Hey, have you seen Jester?”

Nott smirked. “Not in the last couple of minutes.”

Caleb frown. If Nott was involved in whatever Jester was up to, it meant that she was fine. And he was in serious danger. “What is that supposed to mean, Nott?”

Nott played with her button necklace, that shit-eating grin still on her face. “Nothing I can tell you. It would ruin the surprise.”

“So there’s a surprise?”

Nott’s smile fell. “I already said too much. Don’t worry about Jessie, she’s fine. You’ll see it soon enough.”

“How soon?”

She skirted past him and practically ran down the hall. “I’m not at liberty to divulge that information.”

Caleb sighed deeply, his shoulders slumping with defeat. Essek would be arriving soon, so he didn’t have time for more inquiries. This would have to wait until after his lesson, he just hoped he could focus on it with this mystery in the back of his mind.

He made his back to the study and, after quickly arranging his books and stacks of paper, he took a seat, knowing instinctively that he had five minutes until their scheduled time and that Essek would arrive exactly on the dot, as usual.

As he sat back in his chair, he felt something brush up against his leg. He looked under the desk, expecting to see Frumpkin, but there was nothing there. He shook his head, thinking the stress of the last couple of days was making him imagine things, and reached for his quill when he felt it again, this time something caressed his inner thigh and he jumped.

“Sheisse!” As he recoiled, he heard a giggle, playful and warm and unmistakeably Jester’s. “Blueberry?”

“Heeyyy Cay-leb!” She said in a sing song voice, both of her hands coming up to grip is thighs. He felt the pressure, the gentle bite of her nails through the fabric, but he still couldn’t see her.

“What are you doing down there? And why in all the Gods’ names are you invisible?”

“I asked Nott to cast Invisibility on me. Didn’t want Essek to see me down here.” She said like it explained everything.

“Why ever would you want to be under my desk during my Dunamancy lesson?”

She reached for the front of his pants and started unlacing them. “So I can give you a blowjob, of course!”

Caleb felt heat course through his whole body, sinking low between his legs, bringing his cock to life but also turning his cheeks bright crimson.

“Jester, _nein_...” He argued halfheartedly as he felt her hand dip inside his pants. “I can’t, not while Essek is here!”

“Why not? If your self control is so great, you should be able to ignore what I’m doing and keep focused on your class, he wont even know I’m here. I promise I’ll be _very_ quiet if you are...” 

The doorbell rang and Caleb heard Caduceus make his way from the kitchen to the foyer to greet Essek.

“It would incredibly inappropriate!” He hissed as she pulled his pants down just enough to take his cock out. Despite his protests, he pushed his chair closer to the desk so no one could see what was happening bellow his waist. “If he found out it could hurt our relationship with the Dynasty!”

Jester groaned and he could picture her rolling her eyes. “You’re being super dramatic! At most you would both be, like, mega embarrassed for a couple of weeks and then you would make up and get back to your nerdy wizard stuff.”

“Jester...” He sighed as she gave his dick a slow, tentative stroke.

“But that won’t even happen because he won’t find out.”

Caleb shook his head. “I can’t risk it, _Liebling._ ”

He could hear Caduceus make small talk with the Shadowhand just outside of the study and while he knew Essek hated wasting time with those kinds of social pleasantries, he had never been more grateful for how long Caduceus could talk about the local plant life.

From under the desk, Jester shuffled around and let go of his cock. In fact, she must have tucked herself as far back as the desk would allow because she stopped touching him altogether.

“Fine.” She said in her brattiest tone, making him think she was probably giving him an invisible pout. It didn’t make any less effective. “I guess I win the bet then. Go ahead, say you lost, Cayleb.”

“ _Was..?_ Why would this mean I lost?”

“If you admit you can’t handle sitting still and quiet while I suck your dick, then I was right all along. You’re self control is not as good as you think, which means I win!”

Caleb groaned. He had already crossed far more lines to keep wining this bet than he ever thought he would, but this seemed like a step too far. Really, it was a terrible, awful, no good idea... But he couldn’t deny that it was also very hot. He pictured Jester looking up at him from under the desk, her mouth and hands on him, as Essek taught him a new spell, completely unaware of the situation and felt his cock harden.

“ _Nein, nein_ , the bet is still on.” He told her, eyes trained on the study’s door. “I think I can handle it. In fact, I’m sure I can. But you need to promise you won’t make any noise.”

“Didn’t I already?” She said, her tone full of playful enthusiasm once more. “Quiet as a mouse with a mouth full of dick.”

“Jester...” He groaned again but she pounced on him, shutting him up quickly. He heard her crawling forward on the carpet, her skirts rustling quietly, until she was sat between his legs, spreading them wider. She dragged her hands up his thighs and grabbed his dick, not stroking yet, just holding him and letting his anticipation build.

“You can hold on to my horns. Just give them a little tug if I start going too fast.” She took his hand in hers and placed it on her left horn, right at the base where it met her scalp.

“Isn’t this against the rules?” He asked, even though he had already started brushing his finger though the hair around the horn, massaging it in the way she always asked him too whenever she got a headache.

“I’ll allow it, just this once. Trust me, you’re gonna need it.”

Caleb scoffed. “I wouldn’t be so sure about tha-”

Before he could finish the sentence, she ran her tongue over the underside of his length, from the patch of dark auburn hair at the bottom all the way up to his head and Caleb practically convulsed, his hand instinctively clutching her horn, hard. He worried he had hurt her but Jester didn’t even slow down, taking him into her mouth, just as Essek floated in.

“Ah yes, fascinating stuff, Mr. Clay! I wish we could discuss this further but I’m afraid I’m late for Mr. Widogast’s lesson. Another time, yes? Now, if you’ll excuse me...” He shut the door and turned back towards Caleb, who was trying his hardest to sit straight in his chair as Jester started to slowly bob her head, taking more and more of him in with every move. “By the Luxon, that man loves mushrooms!”

“Ah, _ja_... That is our Caduceus for you.” He smiled at the Drow who sat in the chair across from his. “It is nice to see you, Essek. How have you been?”

“Busy, as usual. But so have you, apparently.” He smirked and Caleb became immediately worried that he somehow knew what was going on. Had his face given it away? Did he hear him and Jester speaking through the door? “Mr. Clay told me about the Orcs.”

“Oh, that!” His voice came out high pitched and strained, both by relief and the monumental effort he was making not to move his hips in time with Jester. He rubbed his eyes and cleared his throat, hoping Essek took his odd mannerism as signs of travel exhaustion. “ _Ja_ , we ran into some trouble on the way back. Nothing we couldn’t handle, but troublesome to be sure.”

“No serious injuries, I hope?”

“Beauregard had a very close call. Fortunately, Jester managed to heal her in time.”

“Ah, yes! I keep forgetting Miss Lavorre is a cleric, she always seems to be in the middle of the bloodshed.”

Caleb chuckled. “She’s multi-talented.”

Just then, as if to prove to him just how truly talented she was, in more areas than fighting, Jester pulled back, her fangs scrapping slightly against his skin as she made her way back to his head. She swirled her tongue over and around it, tasting his precum and lavishing where she knew he was most sensitive with all her attention. Caleb clenched his jaw, he refused to let out the moan trapped in his throat but he sighed through his nose. She was going to be the death of him but, by the Gods, he didn’t want her to stop either.

“Are you quite alright, Caleb?” Essek asked.

“Hmm... _ja, ja_ of course!” He mumbled. “Why would you think otherwise?”

“You look a little flustered, like perhaps you have a fever? If you’re not feeing well, maybe we should reschedule our class...”

“ _Nein_ , that won’t be necessary! I-I’m fine!” Without warning, Jester swallowed him back down in one go, all the way until he could feel her nuzzling his lower abdomen, her throat hot and open to welcome him. This time Caleb couldn’t help it, he keened, his hips bucking involuntarily into her mouth, his upper body curling up until he was almost laying on the desk. “Ahh...”

Essek stared worriedly, eyes wide, jaw twitching like he didn’t know what to say. Caleb felt himself go completely red, shame and pleasure mixing in a way that made his brain go deliciously numb. He couldn’t let himself enjoy it, however, not even as Jester hollowed out her cheeks and started milk him at a steady pace.

Caleb knew it was wrong of him, he knew that Essek was attracted to him and he shouldn’t use that to his advantage but he desperately needed to distract him from his odd behaviour. He reached out and placed his hand on Essek’s forearm, rubbing the fabric of his black shirt with his thumb.

“Ah... I do not wish to waste your time, I know how precious it is.”

Essek looked down at his hand and smiled. “Yes, yet you know I’d always make time for you, Caleb.” He put his palm over Caleb’s, running his thumb over Caleb’s knuckles, mirroring the wizard’s caress. “As important as Dunamancy is, your health is more so.”

“I’m fine, truly. It’s just a headache.” He lied, feeling particularly guilty at how much he was enjoying this. If he had any common sense left, he would have told Essek that he really was sick and sent him off, but he was too far gone at this point. “I would very much like you to stay and continue our lesson.”

“As you wish.” Essek let go of him and sat back in his chair. “I let you borrow one of my books last time, did I not? Did you finish it?”

“Oh, ja! It was very interesting although I had some questions about the diagram on page 25...”

They quickly sunk back into their usual roles of teacher and student, Caleb eagerly hanging on every one of his words, thirsty for more knowledge. Jester’s movements fell into a slow and steady pattern that Caleb got used to, breathing through the rolling waves of pleasure, keeping himself easily under control. Just as he got comfortable, however, Jester got bored and started picking up her pace, hands toying with his sack, touching it just lightly enough to leave him frustrated.

Caleb leaned forward to point something out in the book to Essek and took advantage of the position to move his hips in time with Jester, one of his hands reaching under the desk to grab her horn and a fistfull of the hair around it again. She felt her smirk around his length and she gave his balls a firm squeeze. Caleb’s eyes rolled to the back of his head and for a moment he was sure he was going to cum right there. His hips bucked wildly, pushing his cock further down her throat until he felt it spasm around his tip and Jester gagged, loudly.

Caleb’s eyes met Essek’s and he knew the Drow had heard the sound. The surge of panic kept him from orgasming but also left him shaking. He pretended to be having a coughing fit, doubling over in his chair, holding Jester in place so she didn’t move during his award winning performance and got him into any more trouble. When he finally stopped, his eyes were watering and he could hardly catch his breath.

“By the Luxon, you’re really starting to worry me, Caleb!” Essek said, reaching across the desk to touch Caleb’s trembling soot stained fingertips. “Don’t tell me this is just a headache, you’re clearly ill!”

“Y-you’re right.” Caleb lied. “I must have gotten the flue during our trip, you know how fragile Humans are...”

“You should get some rest, maybe ask one of your healers to help you out, yes?”

“Ja, I should... I’m so sorry for-”

Essek laced their fingers together tenderly. “Do not apologise. I came to see you and I have, this was not a waste of my time. Now, do you need help getting into bed? You’re shaking...”

Caleb pictured Essek helping him up and seeing his unlaced pants, his dick hard and wet, slipping from Jester’s invisible mouth, and felt his stomach do a somersault.

“ _NEIN_!” He yelled out. “I’ll be alright, thank you. I just seem to have over exerted myself, I’ll be better in a minute.”

The purse of Essek’s lips told him he didn’t quite believe it but he respected Caleb’s choice. “Very well, I’ll take my leave then. Rest up, my dear. I’ll see you soon!”

Caleb waited until the study’s door closed behind Essek to pull away from the desk and look down at Jester. The invisibility spell was coming to an end and he could see the contours of the horn in his hand already.

“This... was probably the most mortifying moment of my life!” He grunted and Jester burst into laughter.

“Oh yeah? Then why were you so close to cuming?” She asked, pulling his cock from her mouth with an obscene _pop_. “Don’t deny it, I could taste it.”

“You know perfectly well why I was close to cuming, you little minx.” Despite his still racing heart and the embarrassment of the whole thing, he couldn’t help but smile as she became fully visible again.

“I could finish what I started, you know? Unless you don’t find it as fun now that it’s just the two of us...”

Caleb rolled his eyes. “I find it plenty fun, which is why, for the sake of our bet, I’ll have to deny that proposition.”

Jester pouted from between his legs. “Does he always call you ‘my dear’?”

“Essek? Sometimes... Why?” Caleb’s racing heart seemed to trip on itself and come to a standstill for a long, painful moment. “Are you jealous, Blueberry?

“Kinda...” She looked away, her cheeks turning a beautiful shade of purple. “He’s really good looking and smart and you guys have all this wizard stuff in common...”

Caleb was used to being the jealous one and it was not a good look on him. He couldn’t help it when it seemed that everyone who met Jester fell for her, he was afraid of losing her to someone else, someone better. Which, as far as he was concerned, was pretty much anyone else. Knowing that Jester felt like that when he was around Essek elated him and that just proved how terrible of a person he really was. But he didn’t allow himself to wallow in that thought, there would be time for that later.

“Ja, that is true.” Caleb whispered, massaging the base of her horn. “But there’s something he lacks.”

“What?” Jester frowned as she laid her head on his thigh.

“He’s not you, Jester.”

She smiled up at him then, that special small, uncertain smile that broke out when her heart was troubled, the one she only shared with him and Caleb wanted desperately to kiss her. Since he could not and necessity was the mother of all invention, he had an idea. 

“Come here, _Liebling_.” He said, pushing his chair further from the desk. “Get on top of the desk.”

“What?” She asked, even as she did what she was told.

“I want you in my lap but since that would be against the rules of our bet, the desk will do.”

She pushed his papers aside carelessly and sat on the dark wood. As she spread her legs with deliberate slowness, kicking her feet up with glee, Caleb could see she was very much not wearing any underclothes and her slick dripped down her thighs, glistening in the low light.

“So beautiful...” He whispered. He would never not be in awe of her. “Have you been touching yourself under the desk?”

Jester bit her lip and pulled her skirts up higher. “Yeah... What are you going to do about it?”

“Me? I can’t touch you, remember?” He said, arching his brow. “But I know someone who can.”

Jester looked honestly confused, until he started casting. When she saw the ghostly figure of Caleb’s Unseen Servant appear, she grinned.

“You remember Schmidt, don’t you Blueberry?”

She giggled. “Hi, Schmidt!”

“Schmidt, would you like to help Miss Lavorre cum?” The figure had been created to follow rudimentary explicit directions and just stared at Caleb, not sure what he was asking for. “Take her clothes off.”

That he understood and started on his task with methodical, dispassionate, efficiency. It didn’t matter, this wasn’t about him and everyone involved knew it. Jester kept her hungry, anxious gaze locked on Caleb as the figure undressed her, stretching her limbs to help Schmidt out, giving Caleb a show. When the Unseen Servant finally removed her dress and touched her skin, however, her head turned to him and she gasped.

“Cold?” Caleb asked. By now, he had managed to compose himself and tuck his cock back in his pants, although his erection was far from gone.

“The opposite actually. He’s the exact temperature of the room, it’s like touching wind.” She put a hand on Schmidt’s chest and shook her head slowly. “So weird!”

“Do you want me to send him away?”

She smirked. “No. I said it was weird, not that I didn’t like it!”

“Naughty girl.” Caleb chuckled. “Schmidt, start rubbing her clit. Nice and slowly.”

Jester whined as he began stroking her, far slower and gentler than Caleb knew she liked, specially when she was already so wet. Without further instruction, Schmidt kept the same agonizingly slow rhythm, never faltering or tiring, and Jester ended up grinding sloppily against his see-through hand, her own fingers playing roughly with her nipples in a desperate search for climax.

“Schmidt, go faster! _Please!”_ She begged, grabbing one of his shoulders and shaking him roughly, to no avail.

“It’s no use. Only I can control him, _Liebling.”_ Caleb called out from his seat. He had thrown his legs over the arm of the chair and was laying back and watching her with an expression of amused boredom, but the outline of his cock pressing against the fabric of his pants gave him away.

“Then make him go faster!” Jester keened. “Oh, and tell him to finger me! I need it so bad!”

“I don’t think I will. I’m enjoying watching you squirm, _Schatz._ ” He smirked.

“That’s evil!” She pouted. “You’re a wicked man, Caleb Widogast.”

“I’m very aware. But I could get more evil, I could tell him to stop.”

Jester gripped Schmidt’s arm, keeping him close. “Don’t! _Please_ , baby!Fuck, I-ahh!” She was so frustrated at this point that she started slurring her words, her complaints coming off as senseless mewls.

She lifted one leg up onto the desk, spreading herself wider in hopes that the new angle would be enough to get her off and Caleb could see her slick dripping down onto the hard wood surface. But she wasn’t the only one on edge in that room, the sight of her and the sounds of her broken pleading were almost enough to make Caleb cum untouched.

Caleb jumped up from his chair, almost tripping as the sudden bloodrush made his head spin. He closed the distance between him from his Unseen Servant and placed a commanding hand on his shoulder.

“Schmidt, do you want to give Miss Lavorre what she’s been asking for?”

The Servant did not react but Jester’s pleading got louder. “Yes, yes, yes! Thank you, Cay!” She panted, her eyes squeezed shut.

He leaned in over the shade’s shoulder, getting as close as he could to her flushed face without actually touching her. “Don’t thank me just yet, Blueberry.”

Her eyes snapped open and she groaned.

“Patience, _meine Liebe_!” He whispered. “Schmidt needs very clear directions, so I need you to use that talented little mouth of yours and tell me how you want him to make you cum.”

She bit her lip. “What I really want is your cock inside me, Cayleb.”

Caleb shuddered, his resolve wavering, he wanted nothing more than to comply with her demands but there was still that pesky little bet between them...

“Jester...”

“Just tell him to fuck me exactly like you would, baby.” She moaned, stretching forward to run her tongue over his bottom lip.

Fighting back the need to kiss her, he backed away and whispered in Schmidt’s ear, just loud enough for Jester to hear. He knew she loved when he talked dirty, specially because he only did it when he goy too turned on to be self-conscious. And, for better or worse, Caleb had passed that point that day from the moment he had let her put her mouth on him.

“Schmidt, I want you to grab my _Liebling_ ’s hips, shove your cock into her tight little pussy and pound her hard and fast until she cums. Oh, and don’t stop working her clit, got it?”

The figure nodded as Jester keened Caleb’s name, her eyes glassy, lips parted and wet. True to what Caleb had ordered, Schmidt grabbed her roughly before thrusting into her in one smooth motion. It was an odd sight to be sure, but also one of the hottest things Caleb had ever seen. The clear form on the Unseen Servant was almost like a glass dildo, spreading her wide for Caleb’s eyes only. He could see her clench around him as he brought her closer and closer to the edge. At the last moment, Caleb reached for his Servant again and gave him one last order.

“Take your thumb and forefinger and pinch her clit hard. Make my Blueberry cum for me.”

He did and Jester screamed, head thrown back, thighs shaking uncontrollably. Caleb waited until she came down, before ending the spell, leaving the two of them alone again.

“Fuck, I love sex magic!” She mumbled dreamily.

“Can’t say I disagree with that statement. But maybe next time don’t involve Nott in your little plan...”

Jester smirked. “Sure, you just have to teach me how to turn invisible yourself.”

“I don’t think the world could handle the amount of chaos you would get up to with that spell in your arsenal.” He laughed.

“Yeah, but don’t you think that would be pretty hot?”

“Oh, undoubtedly.”

She giggled but her laughter turned into a big yawn. “I think I need a nap after that.”

“That makes two of us, Blueberry.” He said, his body mirroring hers and forcing a yawn out of him as well.

She looked up at the door that led to his room. “Think you can resist cuddling with me if we share your bed?”

He stared openly at her naked, curvy body, flushed and freckled all over. “Not sure, but I’m willing to put that to the test.”

**Notes for the Chapter:**

> This is probably not a correct use of the Unseen Servant spell, but who cares, it's sex magic! I've seen Mage Hand get used a lot but yall know what's better than a hand? An entire, fully controlable invisible body!  
> Next chapter will be Caleb's inevitable loss of the bet, do you have any ideas what could break him after surviving all of this? Fell free to leave it in the comments!  
> As always, Comments and Kudos are so very appreciated!


End file.
